The Ride of Her Life
by thepiratemistress
Summary: Lisa decides to take a train back to Springfield, having graduated from college a year earlier than expected. But a chance encounter on the train makes her realize she still has a lot to learn. Lisa x Bob, Graphic. Rated M for a reason!
1. Chapter 1

Lisa made her way down the train corridor, seeking out her cabin. Her rolling suitcase ambled behind her as she read out the numbers.

"22, 23... 24!" She slid open the door and stepped inside, then groaned. She had been hoping, due mainly to a perceived lack of interest in such an arduous form of travel, that she would be able to have a private cabin. But, judging by the carefully arranged luggage and personal effects around the seating across from hers, this was not to be so.

She sighed. At least the other occupant did not appear slovenly, and that would have to do, she mused, as she set her suitcase upon the rack on the free side.

She sat on the seat for a moment, wondering whether she was going to have to sleep on it like this; it seemed quite cramped. Consulting the pamphlet she received at check-in though, it appeared that the seat folded out into a bed. She wasn't thrilled about that, but she would make the best of it. After all, she was celebrating.

Lisa had just graduated from college. She had opted to stay at school over the previous two summers and, while she missed spending that time with her family, it had given her a chance to take extra classes, giving her enough credits to graduate a year earlier than she would have otherwise. She was going to fly back home and surprise them but, seeing as no one expected her home yet, she decided to take the more leisurely route.

The whistle blew, and the train rumbled as it pulled out of the station. Lisa sat with her legs tucked under her, watching out the window as the view changed from the college town and its surrounding city to the green forest beyond. She gazed unseeingly at the scenery for some time, lost in thought.

As the late afternoon sun settled on the horizon, her stomach let out a long growl. Realizing she hadn't eaten since breakfast, she decided to make her way to the dining car for some dinner.

* * *

Finishing her grilled eggplant panini, Lisa gazed at the wine menu, deciding on a nice red Bordeaux. As she waited for the waiter to return, she watched the other patrons of the dining car.

There were a few couples, some businessmen discussing a mix of contracts and conquests, and a number of lone diners. The table in front of her was empty, but at the next table down sat an individual who had been engrossed in reading a newspaper since she had entered. They appeared to be the only person she noticed who was content to read, and it made her jealous; she wished she had thought to bring a book in there with her. Lisa gazed around for the waiter.

The sound of the newspaper rustling as the individual closed it brought Lisa's attention back to them. But she was not prepared for who it was that was sitting there.

"AHHHHH, SIDESHOW BOB!" Lisa screamed, pointing. She quickly coughed, trying to regain some sense of composure. "Sorry! Sorry!" She laughed nervously addressing the other patrons, who were all staring at her in surprise, disgust, and disbelief. They slowly went back to their business as Lisa closed her eyes and groaned in embarrassment.

"Lisa Simpson? Is that you?" There was surprise, and even a touch of amusement, in his rich baritone.

Lisa opened her eyes and looked at him, smiling and laughing nervously.

"Hello, Bob," she said, her voice coloured by embarrassment.

"Lisa! What are you doing here?" He sounded genuinely intrigued.

"Me? What are _you_ doing here?" There was a touch of incredulity in her voice. Bob laughed and stood, smoothing the front of his suit jacket as he did so.

"May I join you at your table?" He asked with a gesture toward the open seat. Lisa paused for a moment, but then realized she might be gawking.

"O-of course!" She said.

As Bob sat down, the waiter appeared.

"May I get you any desserts or drinks?" He asked them.

"Oh, uh, yes," Lisa faltered momentarily, then cleared her throat. "I'll have the Bordeaux, please."

"Excellent choice," Bob said, as the waiter opened his mouth, presumably to say the same. "Make that two," he added, and the waiter nodded before walking away.

"So, what _are_ you doing here?" Lisa asked. "Last I knew, you were still in Springfield Penitentiary." She grinned nervously, fearing that had been a bit rude, but Bob smiled.

"Ah, that seems like so long ago," he said, sounding a little wistful. "Well, I _was_ in Springfield Penitentiary, until a few years ago. You see, because of my record of attempts at, well, murdering your brother," he grimaced slightly, "I was chosen for a program at another facility; one in Costa Rica."

"Costs Rica?!" Lisa asked with surprise. Bob chuckled.

"Indeed. They have quite advanced medical and correctional facilities there and, because they are not controlled by private interests, they actually work to rehabilitate their citizens."

The waiter arrived with their wine, pouring them each a glass.

"You may leave the bottle," Bob said, and the waiter nodded once more before leaving. "Cheers," he smiled, and Lisa clinked her glass to his before sipping her drink. "Now, where was I? Oh, yes, Costa Rica. I was transferred there as part of a government test evaluating the efficacy of such a program on chronic repeat offenders. I spent three years there, undergoing a series of treatments including various types of therapy. I uncovered many of my underlying issues, and I worked through them; quite successfully, I might add." He paused to sip his wine. "I was evaluated by Costa Rican and American doctors, psychologists, and government officials, deemed fit to renter society, and granted my freedom. I was released six months ago, and I spent some time traveling through Central and South America. I decided it was time to return to Springfield, finally. Only then could I be sure that I am fully recovered."

"Wow," Lisa said. "Do you... think you're cured?" She tried to sound casual, but knew her nervous edge betrayed her. Bob smiled warmly at her.

"I believe I am, but I want to be certain. I can honestly say that it has been years since I last entertained homicidal thoughts about your brother. Seriously!" He smiled genuinely.

"Bob, that's wonderful!" Lisa beamed. "I'm very happy for you," she added, raising her glass to him.

"Thank you," he said, genuinely pleased. "But what about you? You've grown so much since I last saw you; you were what, 8? That much time could not have possibly passed."

"I was 16 the last time I saw you!" Bob almost choked on his wine.

"That's not possible! I recall you being the overly intelligent young girl that... you've... always been..." Bob made an odd face as a realization dawned on him. "I must have always viewed you as being the 8-year-old who foiled my first plan, never allowing myself to really view you differently, even in the few interactions we had where you _weren't_ interfering with my malicious schemes. I do apologize." He had the grace to look sheepish. Lisa smirked amusedly.

"Perfectly understandable," she smiled. "As to what I'm doing here, I'm on my way home to visit my family. I'm surprising them; they don't know that I graduated college a year early."

"Lisa, that is amazing! I feel even more foolish now for not realizing how you've grown. Though, honestly, I must say that I am surprised you did not skip high school altogether and go straight to college."

"B-ob!" Lisa blushed brightly.

"It's the truth, and you know it," he said with stern amusement.

"Thank you," she beamed, and he raised his glass to her.

"Well, it appears that this trip is to be one of celebration for both of us. To you, Lisa, for continuing your journey of academic excellence in a most exemplary fashion." Lisa raised her glass as well.

"And to you, Bob, for exorcising your demons, and preparing to face your past in such an admirable manner. I am truly proud of you." They clinked their glasses again and emptied them.

* * *

Lisa and Bob conversed for some time about her academics, debating their differing viewpoints on a number of subjects, and laughing about the state of general academia. As they neared the end of their second bottle of wine, their conversation had turned toward reminiscing about Springfield.

"I remember when you took over Krusty's show," Lisa said, her head swimming from the wine.

"Ah, yes," he sighed. "The 'Cavalcade of Whimsy'." With a small, unamused chuckle, he rested his chin on his fist and gazed out of the window, not really seeing the passing landscape.

"I really liked that show," she said, her eyes downcast shyly as she sipped her wine.

"Yes, well, our ratings managed to sustain after Krusty left," his face hardened as he continued to look outside. "So long as we showed Itchy and Scratchy, the masses continued to tune in, and-" he stopped abruptly and turned to look at her. "Wait one moment," his face became puzzled, but softened slightly. "You... enjoyed it?" Lisa looked up at him with a bashful grin.

"I did. You brought intellectualism to the imbecilic hordes, while offering them their simplistic vice of senseless cartoon violence as a Pavlovian reward." Bob stared at her for a few long seconds before a bemused grin spread across his face. She smiled back and blushed hard. Bob laughed warmly.

"I must say, it does mean quite a lot to me coming from you of all people."

"Wha?!" She sputtered a bit gormlessly. She cleared her throat. "I mean, why should my minute opinion matter to a mind such as yours? I mean..." she sighed in exasperation, loathing that her ineloquence had shown. Bob let out a hearty laugh, which caused her to turn a further crimson.

"Lisa, please. Your honesty brings a joy to me that I haven't experienced in entirely too long. You don't have to constantly wax eloquent in front of a master of buffoonery such as myself," he said, affecting a haughty air for further comedic value. Lisa giggled.

"Do you still... have the grass skirt and bone necklace?" She smirked, but it was lacking any sarcasm; rather it was concealing something else. Bob quirked an amused brow.

"But of course," he grinned with overly exaggerated lasciviousness. "How could I be the man you see before you without such fineries?"

"I'd like to see it sometime," she tittered.

"I'd like to show it to you," he said in a low purr. Lisa gave him a look of intrigued surprise.

"The dining car is now closed," came an announcement over the speakers. "It will reopen at 6am for breakfast, and we hope you will join us then." They both groaned and rolled their eyes in unison. "Please exit the cabin in an orderly fashion, and have a wonderful night."

"I suppose we should go," Bob said, draining his glass. "I am thankful I had the foresight to bring along a few bottles of wine." Lisa raised her eyebrows, and Bob chuckled deeply. "Would you care to join me?"


	2. Chapter 2

They made their way through the corridor, swaying slightly and laughing.

"Here we are," Bob said, sliding open the door to cabin 24.

"I thought we were going to your room," Lisa said, puzzled. Bob looked at her oddly.

"This _is_ my cabin," he said.

"This is _my_ cabin!" She said, surprised. A grin spread across Bob's face.

"It would seem that fate has once more conspired in our favour." He held the door for Lisa, and she smiled as she stepped inside.

"I am so happy to see that my rose petal has not wilted," Bob said, leaning back after his last sip of their third bottle of wine. Lisa's eyes widened.

"That is one of the sweetest things anyone has said to me," she blushed. "I've often thought about the time we spent together when you were at Monsarno." She looked away shyly and sipped her wine.

"I still don't care for jazz," he said, cracking one eye open amusedly. Lisa tossed a balled up napkin at him, and he laughed. "Remember when we would sing together?" He sighed wistfully.

"Are you saying we make beautiful music together, Bob?" Lisa asked playfully.

"We did quite well at... striking each other's cords in a complementary fashion," he grinned. Lisa blushed and tried to change the subject.

"We always had Walt Whitman; his words were never without remembrance of you."

"Ah, yes," Bob sighed pleasantly. His forehead suddenly creased. "Did you ever have much of a proper childhood?"

"Wha-?" Lisa said, confused by the sudden change of topic.

"I don't mean that as an insult," he said quickly, holding up his free hand in a placating gesture. "Answer me this: How old were you when you began to read?"

"1?" She replied uncertainly. Bob raised an eyebrow.

"And how old were you when you first read Whitman?"

"4...?"

"My dearest Lisa, you and I are so alike," he chuckled. "Sure, we had normal 'parts' of a childhood, such as playing with friends, or going on family outings, yet we oft preferred the company of books. Our imaginary friends were figures from history and literature, and those we created were more of a sparring partner for debates, or soundboards for ideas." Lisa's jaw dropped.

"That is _exactly_ it!" Lisa remembered how much Bob really seemed to understand her on a level few others had.

"That was a part of what I so enjoyed during my time working with Krusty. Was much of it idiotic and simplistic? Absolutely. But, to be able to simply enjoy the childishness of it all..." Bob sighed. "I wish I had spent less time being supercilious and condescending; I wanted to prove that merit should be awarded solely on basis of intelligence, all the while neglecting the basic foundations of life. Words and their structure were more important to me than the vast complexities which underlie emotion."

"I-" Lisa started to argue, but then sighed in frustration. "I'm the same way," she said, her voice soft. "Being the smartest person in the room was always the most important thing to me. It was - _is_ \- my identity; it's what I want to be acknowledged for."

"But to what end?" He asked. "I pride my intelligence, to the point where it has often been my downfall. But, if it were to somehow vanish, what would be left? Who would I be? Who would _you_ be?"

They fell into a silent contemplation, but it was cut short by Bob's amused chuckle.

"I did not mean to make this so morose," he said. "Rather, I intended to segue into something more pleasant and, dare I say, even silly."

"Oh?" Lisa pulled herself from her thoughts. "What did you have in mind?"

A large grin broke across Bob's face as he began to chuckle at his own idea.

* * *

Lisa sat beside Bob on his bed, their backs resting against pillows, and a sheet curtaining them off from the rest of the room. A flashlight rested on another pillow atop a short stack of books between them.

"Oh, Bob," Lisa gasped in excitement. "That is amazing!"

Bob let out a laugh, curling his fingers delicately.

"I always did have a particular affinity for shadow puppets," he chuckled, the wine fueled conversations making his voice raspier.

"You have such long fingers, and you're so good with your hands," Lisa said, realizing the insinuation after she spoke.

Bob's movements faltered, and his spider shadow went askew as he looked at her with raised eyebrows. Her bright red blush was visible even in the low light, and he let out a purring chuckle that made Lisa shiver.

"I've had plenty of practice with my hands," he smirked, and Lisa laughed, still blushing.

"You and me both," she said in an undertone, which seemed to ring out in the small space.

"Perhaps we should do it together," he said in that low purr, and Lisa shivered pleasurably. He picked up the flashlight and the stack of books, moving them aside. "We'll need to be closer for this." He uncrossed his legs and spread them. "Sit here, in front of me."

Lisa's heart was pounding frantically. She moved slowly, pulling her long skirt up to her knees for better mobility as she climbed over his leg, and awkwardly shuffled to sit in front of him. He leaned close to her ear.

"Give me your hands," he whispered, holding his own out on either side of her.

She reached out slowly, embarrassed by how much she was trembling. His long fingers curled around her small hands, and she couldn't conceal her sharp intake of breath. He quietly chuckled, but she could feel it vibrating through him as she leaned close to his body. He had her hook her thumbs together and splay her fingers, palms facing the wall.

"Hold them just like that," he said as he released her hands to grab the flashlight. She tilted her head to see where he was placing it, and laughed as he went to put it into his mouth. He paused his movement. "Have you a better idea?" He questioned, amusement rich in his voice, but Lisa shook her head giggling, and turned to face forward again.

As the flashlight shone over her, she watched the bird-like shadow of her hands display across the wall. Bob reached his hands around, his arms slithering under her own, to rest in front of hers; this caused his body to press more fully against hers. Her breathing stopped as she felt his hard erection against her body. He stilled for a second, his breathing becoming slightly ragged around the flashlight, but he continued with the puppetry. Lisa took a couple of small breaths, trying to keep her trembling at a minimum.

She focused on his hands; the way he brought them up from beneath hers, intertwining his fingers in an odd but delicate manner. She glanced up at the shadow and gasped in awe: He had made the shadow of a woman's figure to rest against her shadow wings, making an angel-fairy type shadow.

"Fwap duh wngs," he spoke around the flashlight, and Lisa grinned, giggling softly.

She moved her hands, making the wings move slowly, in awe that they had made this beautiful creation from something as simple as themselves. She managed to find her voice.

"I think I know why you like shadow puppetry so much," she said softly. "There's so much beauty concealed in the darkness, waiting unseen for but even the faintest light to give it life."

The light shuddered then moved, as Bob dropped the flashlight from his mouth. It landed beside them, still shining at the wall, but no longer across their unchanged hands.

"And, sometimes, the light is there, but simply not in the right direction." He slowly pulled his hands apart and wrapped them around hers, bringing their clasped hands to rest lightly against Lisa's chest.

She was sure he could feel how furiously her heart was thumping as she fought to keep her breathing steady. Though they were already pressed close together, he pulled her closer still, trying to conceal a rough gasp. Her body tight against his, she could feel his erection throbbing against her, and could not keep her breath steady. His hands released hers, and he caressed her arms delicately.

" _As I walk by your side or sit near, or remain in the same room with you_ ," he whispered in her ear, his voice and breathing ragged, " _Little you know the subtle electric fire that for your sake is playing within me_."

Lisa couldn't help the softly gasped moan that escaped her lips. His long fingers gripped her upper arms at the sound, and she felt his hardness twitch involuntarily against her. She turned her head toward him, and their lips met almost instantly.


	3. Chapter 3

There was a spark of deep fire between them the moment their lips touched. The passion for him she had long been repressing spilled forth as she tried to speak of it through her kiss. She twisted in his arms, winding her own around his neck and shoulders, pulling him into a deeper kiss. He pressed his tongue into her eager mouth, and she met it with her own, kissing him with wild lust.

He lifted her up slightly, never breaking the kiss as they slid down into the bed. Her skirt had hiked up her thighs, and one of his legs pressed between hers. She wrapped her free leg around his, pulling him closer still, until his thigh was pressed against her hot sex. He groaned into her mouth and nipped at her lip. Her pleasurable moan caused him to dig his fingers into her back, and she arched forward, her breasts pressing into his chest. Her fingers dug into his lush hair, the nails just grazing the scalp.

He rolled on top of her, one arm trapped behind her back, and the other caressing her small curves. Starting at the exposed skin of her thigh, his long fingers slid up her hip to her stomach; her shirt had ridden up, exposing her pale skin, and he slipped his hand under the fabric. His fingers glided over her ribs, and the hand underneath her twisted slightly, unfastening her bra so that his other hand could move unimpeded to caress the curve of her breast. Lisa moaned as he teased the skin with delicate touches, dancing just around her areola but not yet touching her nipples. She tried turning into his hand, but he pulled his other arm from behind her, and pressed down on her, pinning her to the bed as he chuckled into her mouth.

Releasing her lips, he kissed along her jawline, down to her neck, where he gently nipped at the skin.

"Oh, Bob!" She gasped, and he kissed his way up to her ear.

"I love hearing you say my name," he growled. "Say it again." He pressed his leg harder against her vulva.

"Bobbb!" She moaned, and he chuckled, kissing along her ear.

"I've thought about this, Lisa," he whispered in a low rasp. "I often imagined we'd meet again when you were older; that you would want me; that I would feel you wrapped around me..." He nipped her earlobe and moved so that both of his legs were between hers. "A mind like yours, and a mind like mine... Together in ecstasy... So many nights... I often went to bed with you... Dreaming of this." He pressed his erection against her core, and she gasped. The hand on her breast swept across her hard nipple, and she gasped again.

"I thought of you, too," she whispered, her back arching as he lightly pinched her nipple. At her words, though, his hand stilled.

"Did you really, though?" He asked with a trace of skepticism. Lisa nodded, and he pinched her nipple, eliciting a squeal.

"It started in Italy," she said through heavy breaths. When she didn't continue, he squeezed her nipple gently, rolling it between his fingers.

"Go on," he said against her neck, kissing and sucking lightly.

"I realized-" she paused to moan softly at his ministrations, "-that I was somewhat uncomfortable with knowing you were so far away from Springfield." He slid his free hand into the short sleeve of her top, and pulled down her bra strap, kissing her shoulder and arm along its path. "In the theatre... When you sang Pagliacci... I knew I wanted to hear you sing again..." He released her nipple and pulled his hand from under her shirt. He bit her neck a little sharply, and she gasped. As he began pulling down the other bra strap, she continued.

"I tried not to think about it, but I saw you in my dreams," she groaned softly as he pushed her shirt slowly up her torso, and over her chest. "Some of the dreams were... sexual," she exhaled the word as he removed her bra, exposing her breasts. He gazed at them for a moment, smiling with half-lidded eyes before he began tenderly caressing them both. Lisa moaned. "I read Leaves of Grass... And I imagined hearing his w-words from your m-mouth." She stuttered as his warm breath flowed across one nipple. He chuckled in a low purr.

"I tried not to think about it; to put it out of my mind. But th-" she gasped loudly as his lips closed around one nipple, the tip of his tongue darting forward to tease it. "But then Monsarno happened. You and I... Singing together... Experimenting... It was- I felt so alive with you." One hand was traveling slowly up her inner thigh. "Then you quoted Leaves of Grass to me," her voice was a whisper, lost in the pleasures both real and remembered. "I was so aroused. It felt so wrong, but it was exactly right." His fingertips had travelled almost all the way up her inner thigh; her hips were wanting to buck in response to him being so close. He released her nipple with a pop, and leaned over to the other one, grinning.

"Did you pleasure yourself, Lisa?" His voice was almost a growl. She moaned softly at the sound.

"I perfected the art of pleasuring myself to thoughts of you," she said, her voice now raspy. Bob closed his eyes and moaned aloud, pressing his erection against her roughly. She cried out, arching her back.

"I don't know how much more I can take," he said, his breathing ragged. With a mischievous smirk, Lisa pressed herself against him, and he pulled his hips back, returning the smirk. "I'm just getting started with you," he purred.

He pressed his fingers against her vulva through her panties, and she gasped out a moan, closing her eyes as she threw her head back. He rubbed her gently, enjoying the expression on her face. She whimpered as he stopped, her eyes springing open at once. She opened her mouth to say something, but he slipped his fingers under her sodden underwear, hissing pleasurably as his skin came into contact with his dreams. She let out a panting cry, her hips bucking as he found her clitoris. He shifted his hand, his thumb pressing against her swollen nub while he slid one of his fingers inside her. She was so tight and wet; he shuddered, trying to contain himself. He slid a second finger in, and she ground against his hand, her climax building quickly. He increased the pressure on her clit, determined to take her over the edge.

Lisa's entire body was responding to Bob's touch. She couldn't think straight; it felt as though electricity was coursing through her body, ready to explode. And explode it did. Her back arched deeply, and she gasped, moaning out his name loudly as her entire body convulsed with her climax.

Bob slid his fingers out of her, and she gasped again, her body thrumming with excitement as her senses returned to her. She had never experienced an orgasm from another person. The clumsy schoolboy fondling by Milhouse had been haphazard and uncomfortable, and Nelson didn't bother with foreplay beyond pawing at her breasts.

She smiled at Bob as he lay beside her, and he pulled her close for a deep kiss.

"I hope that was... adequate," he purred against her lips. Lisa scoffed, and he leaned back to give her a puzzled look.

"That was amazing!" She grinned. Bob relaxed and smiled, kissing her gently. She deepened the kiss and pressed her body against his, but he pulled away.

"Apologies, Lisa. It has... been a while for me, and I'm afraid if I do not relax I shall, well, simply _burst_ ," he grimaced slightly. Understanding dawned on her.

"Well, I wouldn't mind _helping_ you with that," she smiled, blushing brightly. He was about to say something when he saw her tongue dart out to lick her lips. His breath caught in his throat.

"You mean... you would... with your... mouth?" He asked, and she blushed brighter, but nodded slowly. "Oh, Lisa," he moaned softly and kissed her.

As she returned the kiss, she felt him moving, and heard the soft unzipping of his suit pants. He broke the kiss to sit up, and she followed him, moving to settle on her knees as she pulled her shirt off the rest of the way. She looked him in the eyes and smiled, then bent down and gasped. Schoolboys had _definitely_ not prepared her for this! Long, with thick protruding veins, Bob's cock was larger than she could have imagined.

Lisa reached out slowly and wrapped her fingers around it. Bob gasped, and she felt him twitch in her hand. She leaned forward slowly, her tongue reaching out to lick the head. He moaned in response, and she took him into her mouth. She could feel him trying to keep his hips steady as she slid her mouth up and down, trying to take more of him in her. He was groaning loudly, one hand buried in her hair, but not controlling her actions.

"Lisa," he gasped, "I can't... I'm going to... oh, mercy, take me!" He cried out, and his hips bucked involuntarily, gagging her as he began ejaculating. Lisa quickly swallowed, sucking him more intensely as his orgasm shot through him. As his climax subsided, Lisa released him with a loud pop. He immediately grabbed her and pulled her into a deep, passionate kiss. "Thank you, Lisa," he sighed as they melted into the bed together. "I cannot recall the last time a woman did that for me. I apologize that it was so quick." Lisa smiled at him.

"I don't know how long I could have lasted," she said sheepishly. "I've never seen a man so big." Bob's arms squeezed her tightly.

"I know I'm... a bit larger than average. Which is why many women have tended to shy away from performing that particular act."

"I didn't mind," Lisa smiled.

Bob kissed her again before shifting to remove his pants and boxers the rest of the way. He sat up and began unbuttoning his dress shirt. As Lisa watched him, she slid off her skirt and panties. Bob looked over her body approvingly as she laid back, propping herself up on her elbows.

"So beautiful..." He tossed his shirt aside and leaned down to kiss her gently.

He started at her lips, then kissed along her jaw and down her neck. As he moved across her chest, he kissed each of her stiff nipples, and the underside of each breast, before traveling over her solar plexus. She let out a small, involuntary giggle as he kissed her smooth stomach, and he smiled, chuckling softly against her skin. He could hear her breath hitching as he kissed below her belly button, and it became more shallow as he reached the top of her pubic mound.

His kisses were feather light as he moved further down, the light hairs tickling his long nose as it travelled through them. His lips paused at the top of her slit, and he smiled as her breathing also stalled. He inhaled deeply through his nose, exhaling the hot breath over her wet vulva, and she let out a quiet gasp.

She whimpered as he kissed delicately, barely grazing her slick nether lips as he made his way to her opening. He paused, breathing heavily against her, enjoying as she squirmed slightly. He extended his tongue slowly; she gasped aloud as he made contact with her skin. He swept his tongue upward, parting her labia, and tried to stifle his own moan as he finally tasted her. She cried out as his tongue slid across her swollen clit, and she unconsciously spread her legs wider.

Bob let out a pleasurable groan and pressed his lips to her clit repeatedly, kissing it tenderly. Lisa moaned and squirmed, but Bob took hold of her hips and held her steady as he wrapped his lips around her clit, massaging it gently. She cried out, twitching in his grip, and he darted his tongue forward, adding it to his ministrations. Lisa gasped aloud, her hips now trying to buck against him. He released his lips and began to lave her swollen button with the center of his tongue. Lisa gripped the sheets and called out his name, her hips threatening to break free from his grasp. He dug his fingers in, holding her firmer as his entire tongue stroked her vulva.

Lisa had never experienced such deft cunnilingus. Her entire body was thrumming, and she felt as though she could barely breathe. Bob slid down, his nose rubbing her clit as his tongue dipped inside of her, and she released the sheets, grabbing his hair as her thighs clamped around his head. Without missing a beat, Bob grabbed her wrists and pinned her thighs down with his forearms. She squealed in a mix of shock and delight; he still had that super strength, after all. A part of her mind contemplated briefly that she should be offended, that she should decry this display of dominant masculinity. But that part of her was quickly silenced as Bob's tongue slithered inside her, tasting her where none had before. She cried out his name, her hips vainly fighting the strong hold he had on her.

She didn't know how much longer she could last. She had never experienced a multiple orgasm with other men - _boys_ , she corrected - and her head was spinning. She was crying out as Bob tongue-fucked her deeply; his tongue alone was better than anything she had experienced inside her before.

It was finally too much to handle. Lisa wailed as the orgasm hit her hard. Bob held fast to her wrists and kept her thighs pinned to the bed as her body tried to break free. He retracted his tongue from her vagina and immediately began lapping at her clit.

"BOB! OH, BOBBBB! FFFFUUUUCCCKKK!" Lisa screamed as yet another climax rolled over the previous, but Bob didn't stop. He pressed his tongue against her harder, releasing one of her wrists so he could press two fingers deep inside her. He curled his fingers upward, rubbing the tips against her g-spot as he continued the ministrations of his tongue.

Lisa dug the fingers of her free hand into Bob's hair, her free thigh pressing his face into her other thigh as yet another orgasm overcame her. She twisted and writhed until she was on top of him, but he had her hooked and she could not escape the pleasure swallowing her whole. Her vision began to go black with the force of the orgasm when Bob pulled his fingers from her and released her other thigh.

Lisa writhed away from him, collapsing face down onto the bed, her limbs writhing in the aftermath of her first multiple orgasm as she gasped, frantically trying to catch her breath. Bob crawled beside her, gently coaxing her until she turned and curled close to him. He stroked her hair and back gently as she took deep breaths, still coming down.

"Bob," she croaked shakily, her voice raw. His deep chuckle rumbled through him and into her.

"I hope that was alright," he smirked. Lisa's head snapped up, her eyes wide as she stared at him.

"That was... I've never experienced anything like that!" she said, still breathing heavily. "Not even close!" Bob let out a low laugh, holding her close.

"I'm not done with you yet," he purred in her ear, pressing his throbbing erection against her gently. Lisa gasped. "If you're up for it, that is," he said gently. Lisa pressed her lips to his neck softly, eliciting a groan from him.

"I'd like to try," she spoke against his skin, and he exhaled pleasurably.

"I'll be gentle," he whispered, pulling her into a kiss. "At first," he grinned against her lips.

She rolled onto her back, pulling him on top of her in the process. Bob settled between her knees and gazed into her eyes.

"Are you sure, Lisa? We can wait..." Bob said, but Lisa was shaking her head before he finished.

"I want you, Bob," she growled.

Bob grinned and leaned down to kiss her. She felt him reach between them, then felt the tip of his erection against her vagina. He broke the kiss and leaned back enough to see her face. He watched her reaction as he slowly began pressing into her.

Lisa's eyes widened as Bob's large cock entered her swollen vagina. She watched his face intently as he watched her; as he pushed deeper he closed his eyes, his mouth forming a large "O" as he stuttered out a gasp of sheer pleasure. Lisa was biting her lip with a groan; she was amazed at how much he was stretching her. His eyes fluttered open before rolling back as he pulled out a bit and then pushed in further, and Lisa wondered briefly if she could take him all.

Bob kept working his length in and out slowly, moving further into her. He sat up a bit and placed his hands under her knees, bending them as he lifted her legs, allowing him to enter her deeper, until he was completely buried in her. He closed his eyes and groaned, reveling in the feeling of her tightly around him.

Lisa's breathing was shallow; she had never felt so full. She gasped as he pulled almost all the way out and slid completely back in, his rumbling moan filling the air.

"Ohhhh, Lisa," he hissed, rocking in and out of her slowly. "Perfect Lisa..."

He increased the pace of his movements, working her in a steady rhythm as they both gasped and moaned.

Lisa couldn't believe how good he felt. Every gentle thrust made her eyes roll back and her back arch, forcing gasp after gasp from her. She could feel a deep pressure that was from more than just Bob's large organ, and she grabbed his shoulders, pulling him closer.

"Bo-obbbbb!" She cried, digging her nails into his back as yet another orgasm tore through her. Bob sped up his movements, drawing out her climax. The sound of his flesh slapping against hers mixed with her loud cries, and his passionate moans joined them.

"Lisa... Lisa!" He growled, pounding her roughly. Her nails were leaving deep gouges in his back, but the pain only heightened his pleasure.

She was wailing out his name in the midst of incoherent half words as another climax rushed over her. Bob could feel his own orgasm building, but he was trying to fight it. He grabbed her shoulders as he hammered his cock into her.

"You like this, Lisa? You like how I fuck you?" He growled out, his breathing labored. She cried out in the affirmative, and Bob moaned, a large grin across his face.

He couldn't hold back any more. He pounded her roughly, his eyes shut tight. Lisa threw her head back as another, stronger orgasm coursed through her.

"Lisa... Lisa... LISAAAAA!" He wailed, his hips bucking against her erratically as he allowed himself to climax, releasing his cum deep inside of her. Lisa's body trembled around him, and his arms shook as they held him over her. He stared into her eyes as they both fought to calm their heavy breathing. Sweat shone on her face, and Bob realized he was dripping with perspiration.

He let out a shuddering gasp as he pulled himself from inside her, and Lisa let out a small whimper. Bob moved to lay beside her and pulled her into his still-shaking arms. Lisa rested her head on his quickly rising chest, listening to his frantic heartbeat.

"That was amazing, Bob," Lisa said, still trying to catch her breath. "I didn't know it could be like that!" Bob's chuckling rumbled through his chest.

"Lisa," he crooned, "you are incredible."

"But I didn't do anything!" She looked up at him, and he laughed, hugging her tight.

"You did more than you know," he smiled, kissing the top of her head. "And that's just the tip of the iceberg, as far as sex goes," he purred softly. Her eyes widened and he chuckled. "Sleep, my rose petal," he said, stifling a yawn.

Lisa stretched to kiss him softly before nestling back against his chest.


	4. Chapter 4

Lisa awoke to the feeling of long fingers stroking her back, as soft humming rumbled through her. She inhaled deeply, the soft smell of natural musk filling her nostrils. She didn't stir just yet, though, trying to place the song floating through her.

"Mmmm," she mumbled with a smile.

"Good morning, sweet Lisa," Bob purred softly.

"Good morning, Bob," Lisa said, her cheeks growing warm. "Was that ' _Someone to Watch Over Me_ ' that you were humming?" Bob chuckled.

"You know me and my Gershwin," he smiled.

"I love that song," she said, looking up to meet his eyes. Bob turned, shifting onto his side, and kissed her softly.

"How are you feeling?" He asked.

"I seem to be feeling alright," she said. "A little sore, perhaps..."

"My apologies-"

"Don't apologize," she blushed further, and Bob pulled her close, kissing her again. Her eyes widened as she felt his erection pressing against her.

"Well, I won't apologize for _that_ ," he smirked, stroking her back some more. "You make me insatiable, Lisa," he said more seriously.

She was at a loss for words. How was it that this wonderful - misunderstood, but still wonderful - man found her so desirable? She decided to worry about that later and kissed him deeply.

Bob was taken by surprise, but he melted into her mouth, his tongue dancing elegantly with hers. He rolled on top of her without breaking the kiss, nestling between her legs once more. Lisa tangled her fingers into Bob's hair, and he moaned into her mouth. Lisa released his lips and kissed along his neck.

"Lisa," Bob whispered, pressing his erection against her, and she gasped. "I want to make love to you."

Lisa stopped kissing his neck and looked up into his eyes.

"Please," she exhaled, pulling him into a kiss once more.

He kissed her passionately as he positioned himself and began entering her slowly. Lisa gasped, still sore from the previous night. Bob worked himself into her carefully, taking long, slow strokes.

This was not like the frenzied lovemaking of the previous night; this was tender and sensual, and Bob wanted them both to feel every minute movement. He rocked gently in and out of her, carefully controlling his breathing and movements. Lisa held him close, kissing him as he slid across her body, her breasts pressed against his chest.

"This feels incredible," she whispered against his lips.

" _You_ are incredible," he whispered in return, increasing his pace a little. Lisa moaned and held him tighter. "Lisa... I don't know how much longer I can last..." he panted.

Lisa rocked her hips against him, and he gasped, looking deep into her eyes. She matched his movements so that they were moving in sync, and Bob groaned loudly. His eyes rolled back as his body stiffened, his hips spasming as he filled her with his semen.

Bob collapsed onto his elbows, resting atop Lisa as he caught his breath. Her body thrummed with adrenaline; she had never made love first thing in the morning, and she told him as much.

"Really?" He looked at her in surprise. She shook her head. "I must say, for being such a bright woman, you appear to have had terrible taste in men," he quipped with a smirk.

"Well, they can't all be you, Bob," she said cheekily. Bob grinned and kissed her nose.

"Come, let us freshen up and grab some breakfast."

* * *

Breakfast had been a rather quiet affair; they shared pieces of a newspaper, while sipping tea and juice, and chasing their burgeoning wine hangovers with plenty of water. They both ate quite heartily, famished from the previous night and that morning's activities, but they didn't speak much beyond pleasantries.

Lisa was mostly lost in her thoughts. She couldn't quite believe that not only was she having breakfast with her brother's mortal enemy, but that she had also experienced some of the most intense pleasure of her life at his hands (and tongue and-); she closed her eyes as her cheeks grew hot.

But she also found herself nervous. How did he feel about it? He seemed to be enjoying her company, but was it just because she was a willing young body for him? They had made such pleasant conversation the previous evening, but was that because of the wine they had both copiously consumed?

She nibbled at a piece of toast, absently watching the passing landscape. They would arrive in Springfield late that afternoon, and this brought more questions to her mind.

What would happen when they arrived? Would he still want to spend time with her, or would he bid her adieu and continue on alone? But, if they continued this... whatever it was... how would people react? How would _Bart_ react? Would her parents try to stop her? And where would he stay? She didn't know his plans beyond returning to Springfield.

She glanced at him and saw that he, too, was gazing out the window as he drank his tea, a pleasantly soft smile on his face as he contemplated his own thoughts. As the mid morning sun shone over him, Lisa studied him.

The hints of his aristocratic parentage were prominent in his high cheekbones, delicate brow, and perfectly symmetrical features. His skin was soft and bright, the slight circles under his eyes were the only thing betraying his hard life. The laugh lines around his mouth along with his faint crow's feet highlighted years of laughter - maniacal or otherwise. His hair seemed to defy both gravity and their tumblings, as it stood out in perfect points of soft curls. His soft smile and half-lidded eyes were the hallmarks of a dreamer. He let out a pleasant sigh, and turned to look at her, startling slightly at seeing her watching him.

Lisa jumped slightly, blushing hard as she quickly looked away, unable to keep herself from smiling shyly. Bob's rumbling chuckle caused her blush to deepen.

"Like what you see?" He purred in amusement. Lisa let out a small titter, and chastised herself mentally. Why did he make her feel like a giggling schoolgirl? She forced herself to meet his eyes, which were full of mirth. She could honestly say that she had never seen him look so happy, even at Monsarno.

"I do," she smiled giddily, wondering if someone had slipped champagne into her juice.

"Shall we return to our cabin?" Lisa wondered if there was something deeper to that question, but his smile was pleasant, with no hint of suggestion. She nodded, wondering if she had wanted it to be more lascivious.

* * *

Bob closed the cabin door behind them and immediately turned, taking Lisa into his arms and kissing her. She returned his passions eagerly, surprising herself. They made their way to his bed, but Lisa's senses seemed to return suddenly, and she stiffened. Bob noticed right away and abruptly stopped.

"Is something the matter, Lisa?" He asked with genuine concern.

"No," she replied at once, but then sighed. "Maybe... I don't know." She sank onto the bed, and Bob stood still, unsure of how to proceed. Lisa fidgeted with her fingers for a moment before looking up at him. _He's so tall_ , she thought briefly before her eyes reached his, and she saw the deep worry there.

"Are you unsure about... last night?" He asked. "And this morning," he added. Lisa shook her head vehemently, then let out a small nervous laugh.

"I don't regret that at all," she said, and he visibly relaxed. "It's just that, well... We're almost back to Springfield," her voice started to trail off as she looked away, but she continued with more conviction. "If that's all there is, and this is just a fleeting tryst, I understand, and I'm trying to keep that in mind. But I can't help but feel like there could be something more." When Bob didn't say anything, she made herself look up at him. His face was a mix of shock, delight, and concern. He slowly sat down beside her.

"I admit that I had been enjoying each moment as it happened, without much thought to beyond this train," he said quietly. "I believe that subconsciously I was hoping that this train ride would never come to an end." He sighed, resting his elbows on his thighs as his shoulders drooped. "I don't know what's out there for me, Lisa; what's waiting for me in Springfield. The most infamous maniac, returning after several years absence. How many will have a panic reaction at seeing me again, much like you did," - Lisa grimaced - "and how many will be willing to accept me as a free and rehabilitated man? How many times will I be forced to recount my treatment in Costa Rica? How much skepticism will I be viewed with at every turn, through every day? Will anyone even believe me?" He finished with a whisper. Lisa's heart ached as she listened to him, and she reached over and rested her hand on his back. He immediately sat up and looked at her.

"And then there's you, Lisa," he said, taking her other hand in both of his. "You have always been a bright spot for me, even before I realized it during our time together at Monsarno. You gave me hope that, while fading at an alarming rate, intellectualism was not yet a casualty. A mind so like my own, but destined to take a better path, and to have a more fulfilling life. You became a sort of beacon of hope for me, and I could always say that I was proud when you foiled my idiotic schemes." Lisa blushed, and Bob reached up to stroke her cheek. "My heart leapt when I saw you here yesterday. To be able to speak with you again, and to see your beautiful face... I realized deep down that I had been returning to Springfield largely with the hopes that you would be there. And then, beyond my wildest imaginings, to have engaged in such passionate coitus with you... I woke up this morning so afraid that I had dreamt it. But seeing you there in my arms, sleeping so peacefully and contentedly without any trace of fear... Lisa, I can't begin to tell you how much that meant to me, specifically that it was _you_ there."

Lisa's heart was racing. "Oh, Bob," was all she could manage to say. She pulled him into a kiss, startling him, but he wrapped his arms around her, deepening it as he tried to show her how he felt.

She climbed onto his lap, pushing him back on the bed as she straddled him and began frantically undoing his shirt buttons. They broke the kiss only momentarily as he pulled her shirt over her head. Their kissing was passionate and intense, both trying to express their need for one another without words as they tore at each other's clothing.

With enough of the offending fabric cleared, Lisa gripped Bob's stiff cock, positioned it at her entrance and sank down onto it. They both cried out against the other's lips in gasping moans, and he grabbed her hips, sliding her back and forth on his large member. Her fingers tangled in his hair as she bit his lips fiercely. He bucked his hips harder against her; their bodies buzzing with ecstasy as she ground against him with more force.

"Bob, oh, Bob! Fuck me, Bob!" She groaned between pants, her teeth digging into his lower lip. Bob was now lifting her with every thrust, crying out her name amidst long strings of Italian and obscenities. His nails were digging into her hips as he hammered into her from below.

Lisa let out a loud guttural wail of his name as her orgasm peaked, and she clamped down around him, gasping out loud moans. It was too much for Bob; he shouted her name with an echoing cry as he pulled her down hard onto his cock, ejaculating deep inside her. Lisa threw her head back, her body shuddering as she cried out in ecstasy.

Her elbows gave out and she collapsed onto his chest, her ragged breathing matching his own. He wrapped his arms around her and held her as they both tried to regain control of their breathing.

As they managed to calm themselves, Lisa lifted her head and kissed Bob. Their kiss was deep and languid, full of passion without a deeper insistence. Bob gasped as she clenched herself around him, still buried inside of her.

"I don't know what Springfield holds for you, Bob," she whispered against his lips, "but I'm not ready to let you go yet."

" _My_ Lisa," he whispered back before resuming their kiss.

* * *

Lisa stepped off the train first, taking a deep breath of the Springfield air. It wasn't the crispest, or the cleanest, or even the most fragrant, but it smelled like home. She glanced around the station; it was somewhat busy - for such a small town, at least - but she didn't see anyone she recognized. She turned to look at Bob, who was waiting just inside the entrance to the train, and smiled reassuringly. His nervousness lessened, and he stepped out to join her.

They made their way through the station rather quickly. Though no one spoke to them, they did notice a few curious whispers in passing. Lisa walked with her head held high, making light conversation with Bob, not bothering to be discreet.

As they reached the street, Lisa hailed a cab, and Bob opened the door to help her in. When he closed the door but made no attempt to join her, she opened it again.

"Aren't you coming?" She asked, confusion written on her face. Bob glanced around momentarily, but then climbed in beside her.


End file.
